New studies of Rh-catalyzed addition of boronic acids under basic conditions in aqueous medium

被引：68

作者：

Amengual, R ^{[1
]}

Michelet, V ^{[1
]}

Genêt, JP ^{[1
]}

机构：

[1] ENSCP, UMR 7573, Lab Synth Select Ogran & Prod Nat, F-75231 Paris 05, France

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 34期

关键词：

water-soluble ligand; boronic acids; alpha; beta-unsaturated ketones; styrene derivatives; recyclable rhodium/m-TPPTC system;

D O I：

10.1016/S0040-4039(02)01274-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rh-catalyzed C-C bond formation in neat water under basic conditions has been efficiently performed. The addition of various boronic acids to styrene, 2-vinylpyridine, and cyclic a,p-unsaturated ketones has been realized with high selectivity and yield. We have shown that m-TPPTC (tris(m-carboxyphenyl)phosphane trilithium salt) exhibited a higher reactivity compared to TPPTS. These couplings could also be conducted very efficiently under basic and phosphaneless conditions to give functionalized aryl derivatives. The benefits of the additional anionic ligand m-TPPTC tied in the successful recycling experiments of 1,4-addition of phenylboronic acid to cyclohexenone, with no loss of the water-soluble catalyst. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：5905 / 5908

页数：4

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